US3615746A - Flame-retardant cellulose triacetate articles - Google Patents
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- US3615746A US3615746A US883997A US3615746DA US3615746A US 3615746 A US3615746 A US 3615746A US 883997 A US883997 A US 883997A US 3615746D A US3615746D A US 3615746DA US 3615746 A US3615746 A US 3615746A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L1/00—Compositions of cellulose, modified cellulose or cellulose derivatives
- C08L1/08—Cellulose derivatives
- C08L1/10—Esters of organic acids, i.e. acylates
- C08L1/12—Cellulose acetate
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- FLAME-RETARDANT CELLULOSE TRIACETATE gg ghf Draw.
- ABSTRACT A composition and solution for forming shaped mgs articles comprising cellulose acetate, from 1 to percent of a [52] U.S. I 106/15, bromo-aliphatic phosphate containing from 10 to 30 percent 106/177, 106/190, 106/196, 251/8.1 bromine and from 0.4 to 3 percent of a second compound [51] Int. Cl C08b 21/04 selected from the group consisting of phenyl phosphates, Field of Search 106/15 FP, cresyl phosphates, di(t-butyl) peroxide, dicumyl peroxide, and
- This invention relates to improved self-extinguishing cellulose triacetate articles, and a process of producing them.
- Cellulose triacetate has found wide commercial acceptance as manmade fibers for textiles, nonwoven products and the like. While these products are for the most part suitable in the end-use applications for which they are utilized, there are uses for which increased flame retardance would be very desirable. Such uses are wearing apparel and household furnishings, such as draperies, and upholstery fabrics.
- lt is a further object of this invention to provide low-denier fiber products of cellulose triacetate which do not support combustion when contacted with a flame after the flame is removed.
- the contemplated phenyl and cresyl phosphates are preferably unsubstituted phosphates having three phenyl or three cresyl groups, e.g. triphenyl phosphate, o-phenylphenyl bis-phenyl phosphate, tricresyl phosphate or tris-o-phenylphenyl phosphate.
- the organic solvent solutions of cellulose triacetate to which this invention may be applied are conventional spinning or casting solutions for the production of filaments and films respectively which generally contain about to 30 percent by weight of cellulose triacetate.
- the solvent used is preferably methylene chloride but other solvents may be used such as ethylene chloride.
- THe bromo-aliphatic phosphate may contain open and/or cyclic aliphatic groups and may be a bromine-substituted alkyl or cycloalkyl phosphate in which the substituted alkyl groups contain 3 to 8 carbon atoms.
- the bromine content of the bromo-aliphatic phosphate is preferably about 10 to 30 percent by weight.
- Some specific compounds which may be used are tris(2,3-dibromo-propyl) phosphate, which is preferred, tris(2,-bromobutyl) phosphate, tris(bromohexyl) phosphate, and tris( bromocyclohexyl) phosphate.
- THe bromo-aliphatic phosphate is used in the solution of cellulose triacetate in an amount of at least 1 percent, preferably 1 to percent, and most preferably in an amount of S to l0 percent by weight of the cellulose triacetate, whereas the second additive compound is used in an amount of 0.4 to 3 percent, preferably 0.4 to 1 percent based on the weight of cellulose triacetate.
- the total amount of additives used is less than the amount of bromo-aliphatic phosphate or second additive compound which would be necessary to produce an equivalent fire-retardant effect in a shaped article (e.g., fiber or film) of cellulose triacetate, when used alone.
- cellulose triacetate is a cellulose acetate containing at least 59 percent preferably at least 61 percent by weight of acetyl group calculated as combined acetic acid.
- cellulose triacetate may be distinguished from secondary cellulose acetate which generally contains about 54 to 56 percent of acetyl groups calculated as combined acetic acid.
- the organic solvent solution of cellulose triacetate may contain other modifying components, e.g., pigments for dulling or coloring the yarn or film, plasticizers, stabilizers, etc.
- Tl-le resulting cellulose triacetate yarn had a total denier of 143, a tendency of 1.33 grams per denier, an elongation of 24.0 percent and was self-extinguishing when subjected to the flame test described below.
- the resulting yarn had a total denier of 75, a tenacity of 1.10 grams per denier, an elongation of 27.5 percent and was self-extinguishing when subjected to the flame test described below.
- EXAMPLE Ill The procedure of example 1 was repeated except that the ophenylphenyl bisphenyl phosphate was replaced by 1 percent based on the weight of cellulose triacetate of di-t-butyl peroxide.
- the resulting yarn had a total denier of 160, a tenacity of grams/denier, an elongation of 26.2 was self-extinguishing using the flame test described below.
- the yarn was knitted into a hose leg, a 6 to 8 inch section of which was suspended vertically from a support placed in an area essentially free from direct air drafts.
- the freely hanging lower edge of the fabric was ignited with a luminous flame from either a Bunsen burner or a paper safety match. After the initial ignition of the fabric, the flame was removed and the burning characteristics of the fabric were observed. The sample was considered to be self-extinguishing if the flame was repeatedly extinguished after several ignitions of the same fabric sample.
- compositions of the invention may also be used to form flame-retardant films and molded articles.
- the organic solvent solution of cellulose triacetate and additives may be cast into films or precipitated to form flake which may subsequently be injectionor compression-molded.
- EXAMPLE Vl In a casting solution of 10 weight percent of cellulose triacetate having an acetyl value of about 6l .5 percent calculated as combined acetic acid in a solvent composed of 91 per- EXAMPLES VII, VIII, IX, X and XI The procedure of example VI was repeated except that the following additives were added to the casting solution in place of 1 percent tris(2,3-dibromopropyl) phosphate and 0.2 percent o-phenylphenyl bisphenyl phosphate:
- Example VII 2% tris(2,3-dibromopropyl) phosphate
- Example VIII l% tris(2,3 dibromopropyl) phosphate and 0.4% o-phenyl phenyl bisphenyl phosphate
- Example IX l% tris(2,3-dibrm0propyl) phosphate and 0.4% tris-ophenylphenyl phosphate
- Example X tris(2,3-dibromopr0pyl) phosphate and 0.4% tricresyl phosphate
- the film of example VII burned when subjected to the flame test described below.
- the films of examples VIII, IX, X and XI were self-extinguishing when subjected to the flame test described below.
- the film was cut into three 3 inch by 6 inch strips held rigid in a metal U-frame.
- the rigid strips were held vertically and ignited with a Bunsen burner. After the initial ignition of the film, the flame was removed and the burning characteristics of the film were observed. The sample was considered to be selfextinguishing if the flame was repeatedly extinguished after several ignitions of the same film sample.
- a composition comprising cellulose triacetate having an acetyl value of at least 59 percent by weight calculated as combined acetic acid, and a flame-retardant amount of a synergistic flame-retardant mixture comprising from 1 percent to 20 percent by weight based on the weight of the cellulose triacetate of a bromo-aliphatic phosphate containing about 10 percent to 30 percent by weight of bromine, said bromoaliphatic phosphate selected from the group consisting of bromine-substituted alkyl and cycloalkyl phosphates wherein said alkyl group contains from 3 to 8 carbon atoms and from 0.4 percent to 3 by weight based on the weight of the cellulose triacetate of a second additive compound selected from the group consisting of phenyl phosphates, cresyl phosphates, di(t-butyl) peroxide, dicumyl peroxide, and 2,5-dimethyl-2,5- di(t-butyl-S-
- composition of claim 1 in the form of a shaped article.
- bromo-aliphatic compound is tris( Z3-dibromopropyl) phosphate and said second additive compound is o-phenylphenyl bisphenyl phosphate.
- bromo-aliphatic phosphate is tris(2,3-dibromopropyl) phosphate and said second additive compound is tricresyl phosphate.
- composition of claim 1 containing from 5 to 10 percent by weight of said bromo-aliphatic phosphate and from 0.4 to 1 percent by weight of said second additive compound.
- tile solution of claim 8 wherein the solvent is principally composed of methylene chloride, said bromo-aliphatic phosphate is tris(2,3-dibromopropyl) phosphate and said second additive compound is a cresyl phosphate.
- composition of claim 8 containing from 5 to 10 percent by weight of said bromo-aliphatic phosphate and from 0.4 to 1 percent by weight of said second additive compound.
- a process for forming a shaped article comprising dissolving in a solvent cellulose triacetate having an acetyl value of at least 59 by weight calculated as combined acetic acid, from I to 20 percent by weight based on the weight of cellulose triacetate of tris(2,3-dibromopropyl) phosphate and from 0.4 to 1 percent by weight based on the weight of cellulose triacetate of a second additive compound selected from the group consisting of phenyl phosphates, cresyl phosphates, di(t-butyl) peroxide, dicumyl peroxide, and 2,5-dimethyl-2,5- di(t-butyl-S-peroxy) hexane.
- a film comprising cellulose triacetate having an acetyl value of at least 59 percent by weight calculated as combined acetic acid, and a flame-retardant amount of a synergistic flame retardant mixture comprising from l to 20 percent by weight based on the weight of the cellulose triacetate of a bromo-aliphatic phosphate containing about 10 to 30 percent by weight of bromine, said bromo-aliphatic phosphate selected from the group consisting of bromine-substituted alkyl and cycloalkyl phosphates wherein said alkyl group contains from 3 to 8 carbon atoms and from 0.2 to 3 percent by weight based on the weight of cellulose triacetate of a second additive compound selected from the group consisting of phenyl phosphates, cresyl phosphates, di(t-butyl) peroxide, dicumyl peroxide, and 2,5-dimethyl2,5-di(t-butyl-5 -peroxy)
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Abstract
A composition and solution for forming shaped articles comprising cellulose acetate, from 1 to 20 percent of a bromoaliphatic phosphate containing from 10 to 30 percent bromine and from 0.4 to 3 percent of a second compound selected from the group consisting of phenyl phosphates, cresyl phosphates, di(tbutyl) peroxide, dicumyl peroxide, and 2,5-dimethyl-2,5-di(tbutyl-5-peroxy) hexane.
Description
United States Patent 1 1 3,615,746
[72] Inventors Willard C. Brinegar [56] References Cited N- UNITED STATES PATENTS gggg? Alma 2,574,515 1 1/1951 Walter et a1. 260/956 [21] 2,675,327 4/1954 Gearhart 106/176 22 1 Filed Dec. 10, 1969 26 1971 2,858,228 /1958 Hughes... 106 190 {g} 22:25:: gg Corporation 3,121,106 2/1964 Nagy 260/952 New York, N Y FOREIGN PATENTS Continuation-in-part of application Sen No, 821,431 10/1959 Great Britain 106/196 562! July 1966 now abandoned Primary Examiner- Lorenzo B. Hayes Attorneys-Thomas J. Morgan, Stephen D. Murphy and Andrew F. Sayko, Jr.
[54] FLAME-RETARDANT CELLULOSE TRIACETATE :gg ghf Draw. ABSTRACT: A composition and solution for forming shaped mgs articles comprising cellulose acetate, from 1 to percent of a [52] U.S. I 106/15, bromo-aliphatic phosphate containing from 10 to 30 percent 106/177, 106/190, 106/196, 251/8.1 bromine and from 0.4 to 3 percent of a second compound [51] Int. Cl C08b 21/04 selected from the group consisting of phenyl phosphates, Field of Search 106/15 FP, cresyl phosphates, di(t-butyl) peroxide, dicumyl peroxide, and
177, 252/8.1; 186/196 2,5-dimethyl-2,5-di(t-butyl-5-peroxy) hexane.
FLAME-RETARDANT CELLULOSE TRIACETATE ARTICLES This invention is a continuation-in-part of U.S. application Ser. No. 562,1 19 filed July 1, 1966 now abandoned.
This invention relates to improved self-extinguishing cellulose triacetate articles, and a process of producing them.
Cellulose triacetate has found wide commercial acceptance as manmade fibers for textiles, nonwoven products and the like. While these products are for the most part suitable in the end-use applications for which they are utilized, there are uses for which increased flame retardance would be very desirable. Such uses are wearing apparel and household furnishings, such as draperies, and upholstery fabrics.
it is an object of this invention to provide shaped articles of cellulose triacetate having increased flameproofing.
lt is a further object of this invention to provide low-denier fiber products of cellulose triacetate which do not support combustion when contacted with a flame after the flame is removed.
It is a still further object of this invention to impart selfextinguishing properties to shaped articles of cellulose triacetate without serious sacrifice of their other favorable properties such as mechanical and dyeing properties.
In accordance with this invention, there is incorporated into an organic solvent solution of cellulose triacetate a minor amount of a bromo-aliphatic phosphate and a minor amount of a second additive compound selected from the group consisting of phenyl phosphates, cresyl phosphates, di(t-butyl) peroxide, dicumyl peroxide and 2,5-dirnethyl-2,5-di(t-butyl-5- peroxy) hexane. The contemplated phenyl and cresyl phosphates are preferably unsubstituted phosphates having three phenyl or three cresyl groups, e.g. triphenyl phosphate, o-phenylphenyl bis-phenyl phosphate, tricresyl phosphate or tris-o-phenylphenyl phosphate.
The organic solvent solutions of cellulose triacetate to which this invention may be applied are conventional spinning or casting solutions for the production of filaments and films respectively which generally contain about to 30 percent by weight of cellulose triacetate. The solvent used is preferably methylene chloride but other solvents may be used such as ethylene chloride.
THe bromo-aliphatic phosphate may contain open and/or cyclic aliphatic groups and may be a bromine-substituted alkyl or cycloalkyl phosphate in which the substituted alkyl groups contain 3 to 8 carbon atoms. The bromine content of the bromo-aliphatic phosphate is preferably about 10 to 30 percent by weight. Some specific compounds which may be used are tris(2,3-dibromo-propyl) phosphate, which is preferred, tris(2,-bromobutyl) phosphate, tris(bromohexyl) phosphate, and tris( bromocyclohexyl) phosphate.
THe bromo-aliphatic phosphate is used in the solution of cellulose triacetate in an amount of at least 1 percent, preferably 1 to percent, and most preferably in an amount of S to l0 percent by weight of the cellulose triacetate, whereas the second additive compound is used in an amount of 0.4 to 3 percent, preferably 0.4 to 1 percent based on the weight of cellulose triacetate.
The total amount of additives used is less than the amount of bromo-aliphatic phosphate or second additive compound which would be necessary to produce an equivalent fire-retardant effect in a shaped article (e.g., fiber or film) of cellulose triacetate, when used alone.
As is well known in the art, cellulose triacetate is a cellulose acetate containing at least 59 percent preferably at least 61 percent by weight of acetyl group calculated as combined acetic acid. Thus, cellulose triacetate may be distinguished from secondary cellulose acetate which generally contains about 54 to 56 percent of acetyl groups calculated as combined acetic acid.
In addition to the flameproofing agents of this invention, the organic solvent solution of cellulose triacetate may contain other modifying components, e.g., pigments for dulling or coloring the yarn or film, plasticizers, stabilizers, etc.
The following examples further illustrate the invention:
EXAMPLE I In a spinning solution of 20 weight percent of cellulose triacetate having an acetyl value of about 61.5 percent calculated as combined acetic acid in a solvent composed of 9l percent methylene chloride and 9 percent methanol were dissolved 5 percent based on the weight of cellulose triacetate of tris(2,3-dibromopropyl) phosphate and 1 percent based on the weight of cellulose triacetate of o-phenyl-phenyl bisphenyl phosphate. This modified spinning solution was extruded in a downward direction through a spinnerette containing 40 holes each 36 microns in diameter into a spinning column of 7 inches in diameter and 7 feet long containing air traveling in an upward direction. The temperature of the spinnerette face was C. and the average air temperature in the spinning column was 50 C. The takeup speed of the resulting yarn was meters per minute.
Tl-le resulting cellulose triacetate yarn had a total denier of 143, a tendency of 1.33 grams per denier, an elongation of 24.0 percent and was self-extinguishing when subjected to the flame test described below.
EXAMPLE I! THe procedure of example I was repeated except that tricresyl phosphate was used in place of O-phenylphenyl bisphenyl phosphate in an amount of 1 percent based on the weight of the cellulose triacetate.
The resulting yarn had a total denier of 75, a tenacity of 1.10 grams per denier, an elongation of 27.5 percent and was self-extinguishing when subjected to the flame test described below.
EXAMPLE Ill The procedure of example 1 was repeated except that the ophenylphenyl bisphenyl phosphate was replaced by 1 percent based on the weight of cellulose triacetate of di-t-butyl peroxide.
The resulting yarn had a total denier of 160, a tenacity of grams/denier, an elongation of 26.2 was self-extinguishing using the flame test described below.
EXAMPLES IV and V The procedure of example 1 is repeated except that the ophenylphenyl bisphenyl phosphate is replaced by 1 percent based on the weight of cellulose triacetate of dicumyl peroxide (example 1V) and 2,5-dimethyl-2,5-di(t-butyl-5-peroxy) hexane (example V).
Satisfactory self-extinguishing yarns are obtained which are self-extinguishing when subjected to the flame test described below. The flame test of the yarn products described in examples I to V was carried out as follows:
The yarn was knitted into a hose leg, a 6 to 8 inch section of which was suspended vertically from a support placed in an area essentially free from direct air drafts. The freely hanging lower edge of the fabric was ignited with a luminous flame from either a Bunsen burner or a paper safety match. After the initial ignition of the fabric, the flame was removed and the burning characteristics of the fabric were observed. The sample was considered to be self-extinguishing if the flame was repeatedly extinguished after several ignitions of the same fabric sample.
Although the foregoing disclosure of the invention primarily described fibers as shaped articles, the compositions of the invention may also be used to form flame-retardant films and molded articles. Thus, the organic solvent solution of cellulose triacetate and additives may be cast into films or precipitated to form flake which may subsequently be injectionor compression-molded. Y
EXAMPLE Vl In a casting solution of 10 weight percent of cellulose triacetate having an acetyl value of about 6l .5 percent calculated as combined acetic acid in a solvent composed of 91 per- EXAMPLES VII, VIII, IX, X and XI The procedure of example VI was repeated except that the following additives were added to the casting solution in place of 1 percent tris(2,3-dibromopropyl) phosphate and 0.2 percent o-phenylphenyl bisphenyl phosphate:
Additives to CTA solution in methylene chloride/methanol Example VII 2% tris(2,3-dibromopropyl) phosphate Example VIII l% tris(2,3 dibromopropyl) phosphate and 0.4% o-phenyl phenyl bisphenyl phosphate Example IX l% tris(2,3-dibrm0propyl) phosphate and 0.4% tris-ophenylphenyl phosphate Example X tris(2,3-dibromopr0pyl) phosphate and 0.4% tricresyl phosphate Example Xl ltris(Z,3-dibromopropyl) phosphate and 0.4% triphenyl phosphate The film of example VII burned when subjected to the flame test described below. The films of examples VIII, IX, X and XI were self-extinguishing when subjected to the flame test described below.
The flame test for the films described in examples VII to Xl was carried out as follows:
The film was cut into three 3 inch by 6 inch strips held rigid in a metal U-frame. The rigid strips were held vertically and ignited with a Bunsen burner. After the initial ignition of the film, the flame was removed and the burning characteristics of the film were observed. The sample was considered to be selfextinguishing if the flame was repeatedly extinguished after several ignitions of the same film sample.
It is to be understood that the foregoing detailed description is given merely by way of illustration and that many variations may be made therein without departing from the spirit of our invention.
The embodiments of the invention in which an exclusive property or privilege is claimed are defined as follows:
1. A composition comprising cellulose triacetate having an acetyl value of at least 59 percent by weight calculated as combined acetic acid, and a flame-retardant amount of a synergistic flame-retardant mixture comprising from 1 percent to 20 percent by weight based on the weight of the cellulose triacetate of a bromo-aliphatic phosphate containing about 10 percent to 30 percent by weight of bromine, said bromoaliphatic phosphate selected from the group consisting of bromine-substituted alkyl and cycloalkyl phosphates wherein said alkyl group contains from 3 to 8 carbon atoms and from 0.4 percent to 3 by weight based on the weight of the cellulose triacetate of a second additive compound selected from the group consisting of phenyl phosphates, cresyl phosphates, di(t-butyl) peroxide, dicumyl peroxide, and 2,5-dimethyl-2,5- di(t-butyl-S-peroxy) hexane.
2. The composition of claim 1 in the form ofa shaped article.
3. The product of claim 2 wherein said shaped article is a fiber.
4. The product of claim 2 wherein said shaped article is a film.
5. The product of claim 1 wherein said bromo-aliphatic compound is tris( Z3-dibromopropyl) phosphate and said second additive compound is o-phenylphenyl bisphenyl phosphate.
6. The product of claim 1 wherein said bromo-aliphatic phosphate is tris(2,3-dibromopropyl) phosphate and said second additive compound is tricresyl phosphate.
7. The composition of claim 1 containing from 5 to 10 percent by weight of said bromo-aliphatic phosphate and from 0.4 to 1 percent by weight of said second additive compound.
8. A solution of cellulose triacetate having an acetyl value of at least 59 percent calculated as combined acetic acid suitable for forming into shaped articles containing from 1 percent to 20 percent by weight based on the weight of cellulose triacetate of bromo-aliphatic phosphate containing about 10 to 30 percent by weight of bromine, said bromo-aliphatic phosphate selected from the group consisting of bromine-substituted alkyl and cycloalkyl phosphates wherein said alkyl group contains from 3 to 8 carbon atoms and from 0.4 to 1 percent by weight based on the weight of cellulose triacetate of a second additive compound selected from the group consisting of phenyl phosphates, cresyl phosphates, di(t-butyl) peroxide, dicumyl peroxide, and 2,5-dimethyl-2.5-di(t-butyl- 5-peroxy) hexane.
9. The solution of claim 8 wherein the solvent is principally composed of methylene chloride, said bromo-aliphatic phosphate is tris(2,3-dibromopropyl) phosphate and said second additive compound is a phenyl phosphate.
10. Tile solution of claim 8 wherein the solvent is principally composed of methylene chloride, said bromo-aliphatic phosphate is tris(2,3-dibromopropyl) phosphate and said second additive compound is a cresyl phosphate.
11. The composition of claim 8 containing from 5 to 10 percent by weight of said bromo-aliphatic phosphate and from 0.4 to 1 percent by weight of said second additive compound.
12. A process for forming a shaped article comprising dissolving in a solvent cellulose triacetate having an acetyl value of at least 59 by weight calculated as combined acetic acid, from I to 20 percent by weight based on the weight of cellulose triacetate of tris(2,3-dibromopropyl) phosphate and from 0.4 to 1 percent by weight based on the weight of cellulose triacetate of a second additive compound selected from the group consisting of phenyl phosphates, cresyl phosphates, di(t-butyl) peroxide, dicumyl peroxide, and 2,5-dimethyl-2,5- di(t-butyl-S-peroxy) hexane.
13. The process of claim 12 wherein said solvent is principally composed of methylene chloride, said second additive compound is o-phenylphenyl bisphenyl phosphate, and said shaped article is a filament.
14. The process of claim 12 wherein said solvent is principally composed of methylene chloride, said second additive compound is tricresyl phosphate, and said shaped article is a filament.
15. The process ofclaim 12 wherein from 5 to 10 percent by weight of said phosphate is dissolved in said solvent.
16. A film comprising cellulose triacetate having an acetyl value of at least 59 percent by weight calculated as combined acetic acid, and a flame-retardant amount of a synergistic flame retardant mixture comprising from l to 20 percent by weight based on the weight of the cellulose triacetate of a bromo-aliphatic phosphate containing about 10 to 30 percent by weight of bromine, said bromo-aliphatic phosphate selected from the group consisting of bromine-substituted alkyl and cycloalkyl phosphates wherein said alkyl group contains from 3 to 8 carbon atoms and from 0.2 to 3 percent by weight based on the weight of cellulose triacetate of a second additive compound selected from the group consisting of phenyl phosphates, cresyl phosphates, di(t-butyl) peroxide, dicumyl peroxide, and 2,5-dimethyl2,5-di(t-butyl-5 -peroxy) hexane.
UNITED STATES PATENT OFFECE Patent 6151.745 Dawd Sci-r1259): rm, 1 m
Inventm-(s) Willard C. Brinegar, Jcseph iiiPietro It is certified that error appears in the above-identified patent and that said Letters Patent are hereby ccrrectec'i as shown below:
Column 3 e X, e" shouii be Calumn 3, Example X1, 1" should be ----l%-- Column 3 65,
Calumn claim 3.2, "59 slwuld ha ----59 percent Signed and sealed this 23rd day of May 1932.
, line 19, "tenfieznc?" should be ---tenacity--- claim 1, "3" should be --3 percent--- Attest:
2311mm: R. ROBERT GOTHSCRQLK attesting 051 new Commissioner 0f Patents
Claims (15)
- 2. The composition of claim 1 in the form of a shaped article.
- 3. The product of claim 2 wherein said shaped article is a fiber.
- 4. The product of claim 2 wherein said shaped article is a film.
- 5. The product of claim 1 wherein said bromo-aliphatic compound is tris(2,3-dibromopropyl) phosphate and said second additive compound is o-phenylphenyl bisphenyl phosphate.
- 6. The product of claim 1 wherein said bromo-aliphatic phosphate is tris(2,3-dibromopropyl) phosphate and said second additive compound is tricresyl phosphate.
- 7. The composition of claim 1 containing from 5 to 10 percent by weight of said bromo-aliphatic phosphate and from 0.4 to 1 percent by weight of said second additive compound.
- 8. A solution of cellulose triacetate having an acetyl value of at least 59 percent calculated as combined acetic acid suitable for forming into shaped articles containing from 1 percent to 20 percent by weight based on the weight of cellulose triacetate of a bromo-aliphatic phosphate containing about 10 to 30 percent by weight of bromine, said bromo-aliphatic phosphate selected from the group consisting of bromine-substituted alkyl and cycloalkyl phosphates wherein said alkyl group contains from 3 to 8 carbon atoms and from 0.4 to 1 percent by weight based on the weight of cellulose triacetate of a second additive compound selected from the group consisting of phenyl phosphates, cresyl phosphates, di(t-butyl) peroxide, dicumyl peroxide, and 2,5-dimethyl-2,5-di(t-butyl-5-peroxy) hexane.
- 9. The solution of claim 8 wherein the solvent is principally composed of methylene chloride, said bromo-aliphatic phosphate is tris(2,3-dibromopropyl) phosphate and said second additive compound is a phenyl phosphate.
- 10. The solution of claim 8 wherein the solvent is principally composed of methylene chloride, said bromo-aliphatic phosphate is tris(2,3-dibromopropyl) phosphate and said second additive compound is a cresyl phosphate.
- 11. The composition of claim 8 containing from 5 to 10 percent by weight of said bromo-aliphatic phosphate and from 0.4 to 1 percent by weight of said second additive compound.
- 12. A process for forming a shaped article comprising dissolving in a solvent cellulose triacetate having an acetyl value of at least 59 percent by weight calculated as combined acetic acid, from 1 to 20 percent by weight based on the weight of cellulose triacetate of tris(2,3-dibromopropyl) phosphate and from 0.4 to 1 percent by weight based on the weight of cellulose triacetate of a second additive compound selected from the group consisting of phenyl phosphates, cresyl phosphates, di(t-butyl) peroxide, dicumyl peroxide, and 2,5-dimethyl-2,5-di(t-butyl-5-peroxy) hexane.
- 13. The process of claim 12 wherein said solvent is principally composed of methylene chloride, said second additive compound is o-phenylphenyl bisphenyl phosphate, and said shaped article is a filament.
- 14. The process of claim 12 wherein said solvent is principally composed of methylene chloride, said second additive compound is tricresyl phosphate, and saId shaped article is a filament.
- 15. The process of claim 12 wherein from 5 to 10 percent by weight of said phosphate is dissolved in said solvent.
- 16. A film comprising cellulose triacetate having an acetyl value of at least 59 percent by weight calculated as combined acetic acid, and a flame-retardant amount of a synergistic flame retardant mixture comprising from 1 to 20 percent by weight based on the weight of the cellulose triacetate of a bromo-aliphatic phosphate containing about 10 to 30 percent by weight of bromine, said bromo-aliphatic phosphate selected from the group consisting of bromine-substituted alkyl and cycloalkyl phosphates wherein said alkyl group contains from 3 to 8 carbon atoms and from 0.2 to 3 percent by weight based on the weight of cellulose triacetate of a second additive compound selected from the group consisting of phenyl phosphates, cresyl phosphates, di(t-butyl) peroxide, dicumyl peroxide, and 2,5-dimethyl-2,5-di(t-butyl-5 -peroxy) hexane.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US88399769A | 1969-12-10 | 1969-12-10 |
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| Publication Number | Publication Date |
|---|---|
| US3615746A true US3615746A (en) | 1971-10-26 |
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| Application Number | Title | Priority Date | Filing Date |
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| US883997A Expired - Lifetime US3615746A (en) | 1969-12-10 | 1969-12-10 | Flame-retardant cellulose triacetate articles |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5219510A (en) * | 1990-09-26 | 1993-06-15 | Eastman Kodak Company | Method of manufacture of cellulose ester film |
| US20120171392A1 (en) * | 2009-09-08 | 2012-07-05 | Sk Innovation Co., Ltd. | Optical Films with Controlled Surface Morphology and the Method of Manufacturing the Same |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2574515A (en) * | 1948-11-26 | 1951-11-13 | Glenn L Martin Co | Organic compounds containing phosphorus and bromine |
| US2675327A (en) * | 1949-11-15 | 1954-04-13 | Eastman Kodak Co | Heat stable plastic composition containing lower fatty acid ester of cellulose |
| US2858228A (en) * | 1956-09-04 | 1958-10-28 | Celanese Corp | Preparation of spinning solutions |
| GB821431A (en) * | 1956-01-11 | 1959-10-07 | British Celanese | Improvements in the manufacture of textile and other materials having a basis of cellulose triacetate |
| US3121106A (en) * | 1960-03-30 | 1964-02-11 | Manufactures De Prod Chim De N | Preparation of halogen substituted phosphoric acid esters |
-
1969
- 1969-12-10 US US883997A patent/US3615746A/en not_active Expired - Lifetime
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2574515A (en) * | 1948-11-26 | 1951-11-13 | Glenn L Martin Co | Organic compounds containing phosphorus and bromine |
| US2675327A (en) * | 1949-11-15 | 1954-04-13 | Eastman Kodak Co | Heat stable plastic composition containing lower fatty acid ester of cellulose |
| GB821431A (en) * | 1956-01-11 | 1959-10-07 | British Celanese | Improvements in the manufacture of textile and other materials having a basis of cellulose triacetate |
| US2858228A (en) * | 1956-09-04 | 1958-10-28 | Celanese Corp | Preparation of spinning solutions |
| US3121106A (en) * | 1960-03-30 | 1964-02-11 | Manufactures De Prod Chim De N | Preparation of halogen substituted phosphoric acid esters |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5219510A (en) * | 1990-09-26 | 1993-06-15 | Eastman Kodak Company | Method of manufacture of cellulose ester film |
| US20120171392A1 (en) * | 2009-09-08 | 2012-07-05 | Sk Innovation Co., Ltd. | Optical Films with Controlled Surface Morphology and the Method of Manufacturing the Same |
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